The Chronicles of Jess and Rory
by browneyedgirl724
Summary: Rory and Jess have never met. They're both 25 and living in New York. Under different circumstances, will their relationship be different? The first two chapter are just a build up, they get longer after that. Please give it a chance and review!
1. Day One

**Background Info: Jess and Rory have never met. They're both 25 and living in New York. If you have any other questions, ask away!**

"_It's the little things that matter that add up in the end with the priceless thrilling magic found only in a friend." –Elizabeth Dunphy_

The first things I noticed: red chucks, long golden brown locks, faded and ripped blue jeans, _Of Mice and Men_, chipped nail polish and blue eyes.

The first time I saw her, she was sitting on a park bench, legs crossed, hair whipping around her and concentrating on a book. I always say it was her red chucks that first drew me to her. I drifted closer and closer, but never actually sat down and spoke to her. On that first day I got close enough to see the title of the book, _Of Mice and Men_, and the chipped red nail polish on her fingers. I also caught a glimpse of her eyes, bright blue…electrifying.


	2. Day Two

"_You always admire what you really don't understand." –Eleanor Roosevelt_

The second things I noticed: a silver locket, The Clash buttons on her messenger bag, _Howl_ and a red dress.

As corny as it sounds, it had to be fate. The second day I saw her in a small coffee shop around the corner from my apartment. She wore a red dress that made her skin glow and her eyes pop. Her hair was tamed in a loose bun. A silver locket hung around her neck and made me wonder who's picture it held. She had a messenger bag slung over her shoulder, the strap was covered with buttons. Familiar The Clash buttons stood out to me. After receiving her coffee she collapsed at a table and pulled out a thin volume. _Howl_. I watched as she became absorbed, but I still didn't speak to her.


	3. Day Three

"_Only when we are no longer afraid do we begin to live." –Dorothy Thompson_

The third thing I noticed: red lips.

I showed up at the same coffee shop on the third day in hopes that she would appear again. I wasn't disappointed. She showed up around six in the evening. I almost chocked on my bagel when I saw her. She wore a black dress that hugged every part of her, there was no doubt she had turned many heads that day. The dress wasn't what was so spectacular though. It was her lips. Bright red. Like she had been drinking red Kool Aid. I couldn't ignore her today. I had to talk to her.

I waited until she was seated with her coffee to approach her. I hesitated and almost chickened out, but I reached her table and cleared my throat. She looked up. God, she was even more striking up close.

"Hello." I started pleasantly. "I just wanted to come over here and tell you that I've noticed you. On Wednesday in the park and yesterday in here. I'd like to get to know you."

"Why?" she questioned tilting her head to the side.

"Because I find you intriguing."

She nodded slowly. "Well, I don't plan on getting in the habit of giving out information about myself to total strangers, but if you can prove you're not a psycho killer, we can get to know each other."

"And how exactly should I do that?"

"That's up to you to decide." She sipped her coffee, watching me over the rim.

"One of the things I noticed about you was that you were reading both times I saw you. _Of Mice and Men_ and _Howl_. I co-own a publishing house/bookstore/art gallery that's a couple blocks from here. How about you stop by tomorrow?" I offered.

"And that will prove you're not a psycho killer?"

"Maybe, unless my business partners decide to start bugging me about buying a bar again, then I might have to become a psycho killer."

She chuckled. "Okay, sounds like a plan."

"Good." I leaned back on my heels. "Do I at least get a name?"

"I don't think so. You can find out so much over the internet with just a name these days. Maybe tomorrow."

"Fair enough." I reached into my jacket pocket and produced a business card. "Here's the address."

"No name." she noted.

"It's not my personal card, and you can find out so much with just a name, I better make sure your not a psycho killer too." I teased.

"Fair enough." She echoed.

"Well, mystery woman, I hope to see you tomorrow." I gave her a smirk and a nod before turning on my heel and exiting the building. Tomorrow would be interesting.


	4. Day Four

_This time I wonder what it feels like_

_To find the one in this life, the one we all dream of_

_But dreams just aren't enough_

_So I'll be waiting for the real thing_

_I'll know it by the feeling_

_The moment when we're meeting will play out like a scene_

_Straight off the silver screen_

_So I'll be holding my own breath right up 'til the end_

_Until that moment when I find the one that I'll spend forever with_

_-Nickelback, Gotta Be Somebody_

Day four: a Yale sweatshirt and a chipped tooth.

I wasn't completely sure she would show up. I busied myself around the store, going over our newest manuscript. It was a tragic love story written by a slightly insane woman in her forties. She had come into the office with her cat in her purse and when Chris kindly asked her to take it outside she let loose a string of curses that left even me speechless. Her writing was decent though.

"Jess Mariano." I looked up from my place sitting on the checkout counter. It was her.

"How do you know my name?"

"I looked the place up, you said you were the co-owner, there's a picture of the owners right on the main page, name and all. And you just confirmed it." She approached me slowly. I took in her appearance. She wore gray skinny jeans and a dark blue Yale sweat shirt.

"Smart."

"Yep." She stopped a few feet in front of me.

"Well this is Truncheon." I gestured around me. "Want a tour?"

"Yeah."

"Okay, this front room is the store with the lounge area over there." I pointed to the big brown couch in the corner next to the table with a coffee maker. I stepped behind the counter. "Back here is the office space. Chris and Matt's desks and my office."

"Why do you get your own office?"

"I didn't at first, but they decided I was scaring away potential authors and artists so they put me in there."

"And what exactly is it that you do?"

"I edit most of our manuscripts. I'm better with the whole grammar thing. We all read over potential manuscripts, Matt handles all the poets and Chris does all the artists. We split all the bookstore stuff evenly." I explained.

"Cool. I like it here." She smiled at me and stepped back out into the store.

"We're considering expanding, moving the office upstairs and opening up the back to use as part of the store."

"What's upstairs now?"

"Matt and Chris live up there."

"Can I have some coffee?"

"Of course. I'll make it."

"I'm gonna look around some."

"Go ahead." I turned around to make the coffee. So far so good. I hadn't scared her away yet, which is always a plus. Once the coffee was done I poured two cups and went to find her. We sat on the couch in the lounge.

"So, have I convinced you I'm not a psycho killer?"

"I think so."

"Does that mean you'll tell me your name now?"

She bit her lip and stuck out her hand, "Rory Gilmore."

"Nice to meet you Rory." I wrapped my hand around hers and squeezed lightly.

"Can I ask you a question?"

"Yes."

"What made you notice me?"

"Honestly? The red Chucks you were wearing."

"Really?"

"Yeah, and then your hair, the book in your hand, your eyes."

She blushed, staring at her hands. "I'm glad you noticed me and came up to me yesterday. I want to get to know you too."

"Do you think we could have dinner tomorrow?"

"I can't do dinner, I'm leaving to head home for a few days, but lunch is possible."

"Lunch then, want to meet here at eleven?"

"That's good for me."

"Good." I leaned back into the couch, smiling at her. She grinned back. "I want to give you something." I told her standing up and heading towards the bookshelves. I scanned the top shelf, pulling out a thin black volume. I retook my seat on the couch, a little bit closer to her this time and handed it to her.

"_The Subsect_…by Jess Mariano." She looked up. "You're a writer?"

"I guess. That's how I got hooked up with Matt and Chris, they owned a small press and agreed to publish it. We turned that small press into this." I gestured to the room around me. "And they became my best friends."

"Wow."

"But that's enough about me, I want to know about you. I assume you went to Yale?"

"You assume correctly."

"What do you do?"

"I'm a journalist, I work for the New York Times."

"Impressive." I leaned closer to her. She smiled at me again, I noticed her front tooth was chipped. Just barely, but it was noticeable. Her phone went off in her bag. She pulled it out, frowning.

"I'm so sorry, but I have to go. There's a problem at work."

"It's alright. I'll see you tomorrow?"

"Yeah. Eleven." She stood up. "I had a good time today, I'll definitely have to come back and go through all the books though."

I laughed, "Anytime."

"Bye Jess."

"Goodbye Rory."

I watched her walk out the door. There was something different about her. Something I felt myself getting addicted to already.


	5. Day Five

"_I love you, not only for what you are, but for who I am when I am with you."_

_-Roy Croft_

Day five: freckles.

She showed up twenty minutes early, wearing a yellow sundress, hair straight, hardly any make up on, beautiful. Matt and Chris were at work today. As she approached me at the counter they ran behind her, hands flying, trying to communicate with me. I glared at them. Matt put a hand to his head and pretended to faint, while Chris caught him. Dumbasses.

"Hi," she smiled at me, leaning against the opposite side of the counter.

"Hey," I returned, catching the scent of her perfume. Strawberry. Today I noticed the dusting of freckles across her shoulders. "Ready to-"

"Hello." Matt popped up at her side. He stuck his hand out. "Matthew Barton, but you can call me Matt. I'm Jess' best friend and business partner."

"No, I'm his best friend." Chris interrupted. "You annoy him." He informed Matt. "Chris Grander."

"Rory Gilmore." She returned. "Nice to meet both of you."

"Okay, guys. We're leaving now." I told them, anxious to get out before they got into story telling mode. I led Rory out of the building, stopping before I shut the door. "And don't burn the place down!" I yelled.

"Your friends are interesting." She said from the bottom of the front steps.

"They're characters, alright."

"They aren't how I would have pictured your friends."

I joined her at the bottom of the steps. "They aren't how I would picture my friends, but they're good guys. They tolerate my mood swings as they put it, give me space when I need, annoy me to no end."

"That's the best kind of friends to have."

"Yeah." I agreed. "Shall we walk or drive? It's about nine blocks."

"Walk, it's a nice day." I started us in the direction of the place I had chosen for lunch.

"So, how long have you been living in New York?"

"How do you know I'm not a native?"

"You don't look like a native or talk like a native and you mentioned you were heading home this afternoon."

"Oh. I've been here for three years, since I graduated college. You?"

"New York born and raised, but I spent a year in Venice Beach, California when I was nineteen."

"Chasing the perfect wave?" she teased.

"No. Getting to know my father, I had never met him before then."

"Ah." She glanced up at me. "There's something we have in common."

"What?"

"Absentee fathers."

"Not exactly the greatest thing to have in common."

"I guess, but looking back I'm kind of glad my dad wasn't around. I wouldn't have the relationship I have with my mother if he had been a constant." She told me.

"In a way I am too, I'm glad he went off and grew up; found the person who will put up with all his crap. I can't say I have a great relationship with my mom because of it though. She wasn't any readier to be a parent than he was, but at least she stuck around."

"Does she still live here?"

"Nah, she moved back to her home town, married a total whack job. He treats her right, he just drives me crazy. She's got her brother there too, she's a lot more stable now." I shoved my hands in my pocket, not completely comfortable with telling her this much.

"My mom was only sixteen when she had me, I think that's a big reason why we're so close. Her parents wanted my mom and dad to get married, but my mom never saw herself with my dad. She ran off with me when I was two, as soon as she hit eighteen. My dad drifted in and out of my life constantly, got married when I was seventeen, and had another kid. His wife ran off to Paris after three years. My mom has almost been married twice and she 's engaged again, to the same guy she was engaged to the second time."

"Why didn't they get married before?"

"He found out he had a kid about a month before the wedding, freak out and shut my mom out. They postponed the wedding, but a couple weeks later, she gave him an ultimatum. Marry her now or don't marry her at all."

"Well you have a very dramatic life."

She laughed. "I guess I do."

"And here we are." I told her, gesturing to the building on the corner in front of us.

"Oh my God, my mother is going to have a heart attack when I tell her I came here. She's been begging me to bring her since I moved here. We love Seinfeld."

"I do too." We were in front of the door now. I opened it for her. "After you."

"Thank you."

I followed her inside. "Any seating preference?"

"No, you pick." She told me. I led her over to a booth by the window. She slid into the seat across from me. A waitress approached us.

"Hi, I'm Jenifer and I'll be serving you today." She placed a menu in front of each of us. "What can I get you to drink?"

"I'll have a coke please." Rory said.

"Make that two."

"Okay, I'll be right back." She disappeared. We both scanned our menus, me glancing up at her occasionally.

"What?" she asked after a few minutes.

"What what?"

"You keep looking at me."

I looked down, embarrassed at being caught. "Nothing." I said with a small grin. Jenifer appeared again, saving me from further questioning. She set down our drinks.

"Are you guys ready to order?"

"Ror?" I questioned looking up at her.

"Um, yeah." She answered. Jenifer poised her pen. "I'll have the Cheeseburger Deluxe, but can I have the fries with melted cheese?"

"Of course. American, Swiss or Mozzarella?"

"American."

"Okay, and you sir?"

"I'll have the Chicken Cutlet Deluxe."

"Is that it?"

"Yes, but we'll need to place a to go order before we leave."

"Alright." She nodded and walked off.

"Matt and Chris?" Rory questioned.

"No. You're taking your mom something."

"Okay." She smiled. "Next time she's here we're going to come here and you're coming and bringing Matt and Chris. She'll love them."

"Deal."

"I read your book." She told me after a moment of silence.

"Already?"

"Yeah, I couldn't put it down. It's amazing."

"It's not that great."

"Don't be so humble. I'm buying another copy before I leave today so I can give it to my grandpa while I'm home."

"I'll give you one."

"That's not necessary, I'll buy one."

"You're spreading it around, the least I can do is give you a copy."

"You already did."

"Well I'm giving you another."

"Jess-" she was cut off when our food arrived. We both dug in and she amazed me with how much she could eat, finishing off all of her food and half of my fries. She ordered her mom something and after a brief debate, which I won, over who would be paying for her mom's food we left. The walk back to Truncheon was brief and filled with chat about books, music and movies. We exchanged numbers and she promised to stop by Truncheon one day next week, when she got back to the city. I hugged her and watched her drive off, missing her already.


	6. Day Ten

_"I wished for nothing beyond her smile, and to walk with her thus, hand in hand, along a sun-warmed, flower-bordered path." –Andre Gide_

Day ten: legs.

I hadn't seen Rory since we had lunch on Sunday, but she had called. Twice. Once Sunday night to tell me she had gotten home safely and that her mom loved the food then again Wednesday to tell me she would be home Friday morning and ask if she could stop by the bookstore. I said it was perfectly fine with me. She told me she would be in about noon.

It was now eleven thirty. Matt and Chris were hovering near the front of the store.

"Will you two cut it out!" I snapped. They looked up.

"We aren't doing anything." Matt answered quickly. "We're just waiting for your girlfriend to show up. As your best friends we have the right to get to know her."

"She's not my girlfriend. And if you two don't get your asses in the back and start working I'll evict you." I pointed an invoice at them, my voice dead serious. They frowned and headed for the back. Of course they knew I wasn't really mad at them. This was how we operated, they goofed off and I threatened them to motivate them. When she got here they would sneak back out. I didn't care, I just couldn't deal with them acting all squirrely while I was trying to get some work done. You'd think they were the ones dating her.

She showed up a little after noon; clad in short jean shorts and a The Clash Revolution Rock t-shirt. Her hair was up in a loose ponytail and from what I could tell she wore no makeup. She definitely had nice legs.

"Hey," she slipped behind the counter and greeted me with a hug which I quickly returned. She took a step back smiling. "I feel underdressed." She said gesturing to my clothes.

"No, not at all, you look great. I would prefer to be more casual, but I've got to work."

"Well, you've got a little piece of heaven to work in so it can't be so bad."

"Yeah," I leaned closer to her, like I was telling her a secret. "I kinda love it."

"I would say you were certifiable if you didn't." She looked up at me. Our faces were only inches apart. "If you have work to do, I'm going to look around some"

"Okay." I nodded and watched her walk away. Damn.

I felt a hand on my shoulder. "Stop drooling, pup." Matt said, knocking me under the chin.

I scowled at him. "You go anywhere near her and you'll be eating through a straw."

"I consider myself warned."

"Good." I turned back to my paperwork.

"I can do that for you." Matt pointed to the papers in my hand.

"Really?"

"Yeah, go hang with your girl."

"Thanks." I patted him on the back. It didn't take long to find Rory. She was sitting on the floor leaning against the wall, in between book shelves. She had a book in hand and a small pile next to her. I watched from a few feet away as she read the back of the book. Her nose was scrunched up and her eyebrows knitted together. With a sigh she placed the book back on the shelf and began browsing again. I laughed softly and she looked up.

"Oh, hi."

"I leave you alone for three minutes and you already have four books."

"You guys have a great selection. I haven't been able to find this in any stores." She held up a copy of _Please Kill Me_. I took it from her and put it back on the shelf.

"Don't get that. You can borrow my copy, its better."

"For a business man you suck at business." She leaned in. "Little tip, you aren't supposed to talk people out of buying books."

"I know, but my copy _is _better."

"Fine." She rolled her eyes playfully and held up her other selections. "Am I allowed to buy these?"

I inspected them, "Yeah."

She laughed, leaning against the bookshelf. "Are you working this weekend?"

"Probably not."

"What about Monday and Tuesday?"

"I don't know. Why?"

"My best friend and her husband are coming up tonight and we're heading to Coney Island until Tuesday. Would you be interested in joining us?"

"I have to check with the guys about Monday and Tuesday, but I'd love to." I smiled down at her. "Is your friend okay with it?"

"Yep."

"Okay. I'll go talk to Matt and Chris, now." I headed to the back, grabbing Matt's arm along the way and pulling him with me.

"What are you grinning about?" Chris asked.

I hopped on top of Matt's desk, facing both of them. "Can you guys cover the store and everything until Tuesday?"

"Why?"

"Rory invited me to Coney Island."

"Aw." Matt put a hand over his heart. "How sweet."

I kicked him in the back of the leg. "Yes or no?"

"We can cover it. You never take any time off anyway." Chris said.

"Thanks. I'll probably head out early today."

"No problem."

I patted them both on the back, smacking the back of Matt's head too and headed back out to find Rory. She was leaning against one of the shelves, waiting.

"They said they could cover it."

"So that's a yes?"

"That's a yes."

"Good."

"When are we leaving?"

"Tomorrow morning. Lane and Zach won't be up until later tonight, they have practice, so we decided to wait. We're gonna drive, I guess we'll pick you up."

"I'll give you my address, I live right around the corner." I grabbed a piece of paper out from under the counter. "What are they practicing for?

"They're in a band."

"Cool, anyone I've heard of?"

"Maybe. Hep Alien?"

"Yeah, I saw them at CBGB's a few years ago."

"It took them forever to actually play that gig, it got rescheduled at least four times. Like 'em?"

"They were good." I handed her the slip of paper with my address on it. She set her books on the counter.

"I should probably get going. I've still got some packing to do and so do you."

"Yeah." I rang up the books, handing her a paper bag with her purchases. "I'll bring _Please Kill Me_ tomorrow." We walked towards the door.

"Okay, thanks." She stopped before exiting to hug me. "I'll see you tomorrow morning, about seven."

"Alright."

"Bye Jess."

"Goodbye Rory." I shut the door behind her. I exited the building a few minutes after her, hurrying home. I had packing to do.


	7. Day Fifteen

**Update note:**

**It certainly has been a while, hasn't it?**

**I've been gone for two years, which is unbelievable to me. I started this the summer after my freshman year of high school. I lost a friend to suicide not very long after I posted this, and to be honest that is what stopped my writing. I spent that summer healing. And when school started back up, I threw myself into it completely. I dedicated all of my time to Newspaper and Yearbook and fell in love with both. That love and the all in effort I put forth as a sophomore led to me being Editor in Chief of both as a junior. On top of the huge responsibility of being Student Government President. I honestly don't know what I was thinking. I didn't have time for anything. But it was probably the greatest year of my life. And the worst, in some ways. Now, I'm preparing to be a part time senior, part time college student in the fall. I'm happy again. I want this outlet back, I want the passion I had for writing back. Especially for this story.**

**To any old readers still out there in Gilmore Girl fan fiction world: I really do apologize for my time away, but it was much needed. Stick with me while I try to get back into the swing of things.  
**

**To new readers: Hi! I promise to try not to disappear into oblivion this time around.**

_"The most important thing in life is to learn how to give out love, and to let it come in." -Morrie Schwartz_

_Day Fifteen: Coconut_

I had been two weeks since I first spoke to Rory. Two amazing weeks. I had never cared about a girl like this before. That terrified me and put a goofy grin on my face at the same time. As a twenty-five year old man who had been in countless relationships, I had never gone away with any girlfriend. But Coney Island was one of the greatest weekends of my life. And hell, she wasn't even my girlfriend yet. Her friends, Lane and Zach, were exactly the kind of people I loved. Eccentric. Parents of two sets of twins who played rock shows every weekend. I found myself laughing at the stories of potty training while on tour, or a show that didn't go on because Kwan was turning into quite the klepto. I could see myself spending future time with these people, or even their kids.

I was comfortable, something that didn't happen too often. We had fallen into a strange rhythm of late night phone calls and early morning coffee dates. I learned that her eyes flashed almost silver when she was excited, or turned the deepest shade of navy when she was angry. I began to think that I would never understand how the girl could curse like a sailor and speak bluntly about anything, but my subtle innuendos managed to set her cheeks on fire in the most adorable way. I looked forward to the way her feet shuffled and her head fell when she blushed in embarrassment.

I looked up as the most beautiful half-dead looking girl I had ever seen slid into the seat across from me and began inhaling the coffee I had waiting.

"So early." She grumbled almost incoherently. Her eyes were closed and her head was leaned back.

I smiled. "You've got to go catch that journalistic worm."

"Screw the worm." She opened her eyes. "I'll trade jobs with you."

"I'll pass, sorry."

She shook her head, while downing the rest of the cup. "You're still planning on coming Friday, right?"

Friday. The online magazine she worked for on the side was expanding to print. Big launch party.

"Of course." I smiled. "Is your mom still coming?"

"Yes, she's throwing a fit about not being my only date, but she's coming."

Date. Huh.

"Why don't you ask Matthew to take her? With all the stories you've told, he's practically counting down to meet her."

"That's a really good idea." She pondered. "I should clear it with her first though. She is engaged and all." She paused. "Not that she'd go after Matt, he's a little young. But there was the one time she dated a kid from her business class. He was barely older than me…I'm rambling, sorry."

I reached for her hand, lacing our fingers together across the table. "I'll listen to you ramble all day if that's what you want to do."

"Oh, I wish, but I really should go get that worm." She smiled, tilting her head and squeezing my hand. "I'll talk to Mom and call you while I'm at lunch."

"Okay." We stood. I pulled her into my embrace, noting the sweet coconut smell her hair held.

A smile. "Bye, Jess."

"Goodbye Rory."


End file.
